Aluminium lithium hydride → 2-Benzyloctahydro-1H-pyrrolo[3,4-c]pyridine

HRID 253181Notes

Reaction equation

HRID 253181 reaction equation
[CH2:1]([N:8]1[CH2:16][CH:15]2[CH:10]([C:11](=O)[NH:12][CH2:13][CH2:14]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:8]1[CH2:16][CH:15]2[CH:10]([CH2:11][NH:12][CH2:13][CH2:14]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66846774HCID 66846774, compound

Product 1

HCID 219789862-Benzyloctahydro-1H-pyrrolo[3,4-c]pyridineYield 102.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the lactam from Example 22C (0.46 g) in THF (5 mL) was added 1M LiAlH4 (4.0 mL). The mixture was heated at 50° C. for 2 h, cooled to 15° C., and quenched by cautious addition of water (0.15 mL), followed by 15% NaOH (0.15 mL), then water (0.456 mL). The mixture was stirred for 5 minutes and filtered and washed with THF (3×5 mL). The filtrate was concentrated in vacuo to afford 442 mg of the title compound as a clear oil (quantitative yield). MS (CI) m/z 217 (M+H)+; 1H NMR: δ 1.8-1.5 (m, 3H), 2.33-2.10 (m, 2H), 2.8-2.4 (m, 8H), 3.75 (s, 2H), 7.25 ppm (m, 5H).

Workup

  1. temperaturecooled to 15° C.
  2. customquenched by cautious addition of water (0.15 mL)
  3. filtrationfiltered
  4. washwashed with THF (3×5 mL)
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1999b5c21a8746d19205e84693954fdc
Source dataset
uspto-grants-2011_01
Patent number
US07872010B2

Reaction notes

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